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<h1><a href="https://archiveofourown.org/works/26870602">History Repeats</a> by <a class='authorlink' href='https://archiveofourown.org/users/Tigerfics/pseuds/Tigerfics'>Tigerfics</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Original Work</td></tr>

<tr><td><b>Genre:</b></td><td>Extremely Underage, F/M, Implied/Referenced Incest, Kinda, Rape/Non-con Elements, Toddlercon, Underage Rape/Non-con</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-23</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-23</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 19:14:42</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Rape/Non-Con, Underage</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>2,565</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/26870602</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Tigerfics/pseuds/Tigerfics</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>Their first time together isn’t actually their first.</p>
            </div></td></tr>

<tr><td><b>Comments:</b></td><td>8</td></tr>

<tr><td><b>Kudos:</b></td><td>58</td></tr>

</table>

<a name="section0001"><h2>History Repeats</h2></a>
<div class="story"><div class="fff_chapter_notes fff_head_notes"><b>Author's Note:</b><blockquote class="userstuff">
      <p>This is FICTION! Enjoy!</p>
    </blockquote></div><div class="userstuff module">
    
    <p>The day after her eighteenth birthday, Jailyn Trent spends an hour on the train before walking two blocks towards a lavish hotel. As soon as she enters the beautifully appointed lobby she nervously looks around, her eyes finally falling upon a tall man in a sharp dark blue suit. She grins as relief washes over her. “Maddox!” She quickly walks to him and he envelops her in a tight hug before capturing her lips in a passionate kiss, their first. 
</p>
<p>—————————————————————————————</p>
<p>They met online and had known each other for nearly two years before finally planning to meet in person, much to Jailyn’s disappointment. She’d tried to convince Maddox to meet her after six months but he always refused, wanting to wait until she’s of legal age before they move their relationship to the next level. He’s been a perfect gentleman the entire time, even when Jailyn begged him to loosen up. Whenever her begging and attempts at coercion reached too far he’d remind her that the last thing he wanted was to take advantage of her, and that anyone seeing them together would immediately question the age difference. </p>
<p>The only time he’d ever slipped up was the night of his fortieth birthday when his friends had taken him out for drinks and he’d had one too many. At the end of the night Jailyn had FaceTimed him as per their usual nightly routine. She’d surprised him by wearing a sexy negligee, the silky turquoise fabric draped beautifully over her dark brown skin. Maddox’s normally air-tight self control had buckled at the beautiful sight before him, his hand immediately reaching to rub at his rapidly hardening cock through his pants. </p>
<p>That night he watched her bring herself to orgasm, her soft voice begging him to fuck her in between ragged moans. He’d told her to call him “daddy” and she’s shamelessly called him that every night since while trying to get him to crack a second time, but he’s held strong. </p>
<p>—————————————————————————————</p>
<p>The pair hold hands the entire elevator ride up to the tenth floor, Jailyn curled closely against Maddox’s side. As soon as the door to their room closes behind them Maddox has her pressed back up against it, his lips crashing down onto hers with all the passion he’s been holding back for what feels like forever. He undresses her slowly, pressing kisses to each inch of smooth skin as it’s revealed. By the time Jailyn is completely nude her skin is on fire from his mouth and his hands. </p>
<p>“I’m ready, Maddox, please, I need to feel you inside of me!” 

</p>
<p>He pulls her into a tight embrace and spends long minutes kissing her, keeping her in his arms when she attempts to pull away. “Shhh baby, slow down. We’ve got the entire weekend, I don’t want to rush this.” He kisses her deeply one more time before taking her by the hand. Maddox leads her to the bed and urges her to lay down in the middle. “Do you trust me?” </p>
<p>Jailyn nods. “Of course I do, I love you.” </p>
<p>Maddox kneels beside her and kisses her again, softly this time. He pulls back just enough to meet her gaze. “You have no idea how much you mean to me Jailyn, I love you too.” He reaches toward the headboard and pulls one end of a silk scarf he’d tied there earlier. He trails the end over Jailyn’s wrist and she startles at the unexpected sensation. When she sees what Maddox is holding she laughs, but otherwise doesn’t comment, just moves her wrist closer to the headboard. </p>
<p>Once he’s secured all four of her limbs Maddox stands and removes his own clothing. He does so quickly, taking nowhere near as much care as he had when removing Jailyn’s. He returns to the bed once he’s finished, laying on his side next facing her. </p>
<p>“I’ve got something to show you, something I made just for you.” </p>
<p>Jailyn tilts her head in confusion as he reaches for the remote that’s on the small wooden bedside table. He turns on the tv screen and the DVD player, and in under a minute the black screen flickers to life with the frozen image of a dark bedroom. Maddox presses play and the image begins to move, shadows moving in the doorway before the light turns on, illuminating the room. </p>
<p>Jailyn freezes when a much younger version of herself walks into the frame and sits on the bed. Her hair is shorter and pulled into a frizzy bun, purple butterfly clips shining as she moves. If she had to guess she’d say she was around 2 years old at the time. Just as she’s about to ask what’s going on her eyes widen in shock. On the screen Maddox enters the room and kneels in front of her younger self. </p>
<p>“What the fuck is happening?” She asks, jerking her arms within her binds. “Take these off Maddox, this isn’t funny.” </p>
<p>He shushes her, stroking her hair as his eyes are glued to the tv. “Just watch baby, I don’t want you to miss anything.” </p>
<p>On the screen Maddox is helping Jailyn remove her clothes, talking too softly for the camera to pick up more than an occasional encouraging word. Once every inch of her delicate skin is bare he quickly removes his own clothing and tosses it to the side carelessly, his eyes moving hungrily over the tempting sight before him. </p>
<p>Wordlessly he reaches for her, cupping a hand gently behind her neck and guiding her closer. The girl’s eyes are confused but she moves as he directs, entirely trusting. With his free hand Maddox grips her hair and pulls her head forward until her lips are rubbing against his leaking cock. </p>
<p>“Open for Daddy, Jailyn,” he orders, pulling her head closer. She purses her lips tight and turns her head to the side so his cock leaves a sticky trail of precum along her cheek. Maddox sighs and brings his hand to her chin, gripping tightly. “Open. Or I’ll have to do it for you and I promise it will hurt.” The girl squeezes her eyes shut as her mouth opens the barest amount. Maddox presses his hips forward until his cock is resting on her plump bottom lip. He circles his hips, tracing her lips and leaving a light sheen of precum. </p>
<p>Without warning he thrusts his hips forward, his cock hitting the back of Jailyn’s throat. She tries to jerk back in surprise but his hands hold her in place. When she instinctively tries to close her mouth he holds her lower jaw open, pressing his thumb into the hinge hard enough that tears begin to well up in her eyes. </p>
<p>Maddox’s hips find a leisurely pace, going just deep enough to brush the back of Jailyn’s throat on every other thrust. He throws his head back in pleasure as he fucks the two year old’s face, her quiet sobs interrupted by an occasional gagging noise. </p>
<p>Eighteen year old Jailyn thrashes about on the bed, her screams drowning out the noises her younger self is making on the tv. Maddox grabs her by the chin, much like they both just watched him do on the recording. “If you don’t shut up I’m going to have to make you.” His hand trails down to her throat, his grip tightening. “Are you that desperate to gag on my cock again?” He rubs his thumb over her lips, just barely pressing inside to feel the same incredible heat he felt 16 years ago. </p>
<p>“Watch the video, Jailyn. Or I’ll restart it and you’ll have to rewatch the entire thing.” </p>
<p>When they both redirect their attention to the tv their younger selves have repositioned, little Jailyn laying down on the bed with Maddox between her legs. He’s holding both of her thighs so she’s spread open, and though it isn’t visible in the recording, the sounds coming from the tv make it obvious that his mouth is pressed to Jailyn’s tiny cunt. She’s twitching and moaning, obviously overwhelmed with the new sensations. Her thighs are shaking and were it not for the strong hands holding them up they’d likely be clamped tightly around Maddox’s ears. </p>
<p>Maddox’s mouth waters as he watches himself devour the toddler on screen. He reaches for the similarly bared cunt before him, running two fingers over the slick opening. “You were my first, Jailyn. And my favorite. Just look at how much you loved my mouth on your sweet little pussy.” He slides a finger into her at the exact moment his younger self does the same on screen. “You took that first finger so beautifully, just like you are right now.” He twists to look her in the eyes as he adds a second finger. “Do you know what it does to me to know that I’m the only person that’s been inside this perfect body? That you opened up for me at two years old and again at eighteen, and there’s been no one in between.” </p>
<p>“Why are you doing this?” Tears are streaming down Jailyn’s face, her eyes moving between the man in next to her and the one abusing her younger self. “Why me?” </p>
<p>Maddox grins widely, rolling on top of her bound body. Their skin is nearly the exact same shade, making it hard to see where Jailyn ends and he begins. His hard cock presses between her spread thighs, leaving a trail of precum on his own knuckles where his fingers are still fucking into her. “Because you’re mine.” He pulls his hand out from between her legs and positions his cock there instead. “Look at the screen Jailyn.” </p>
<p>She shifts her eyes back to the screen and watches helplessly as Maddox holds her younger self down and forces his cock into her impossibly small vagina at the exact same moment the Maddox currently on top of her pushes inside. The screams of her on the recording blend seamlessly into her screams in present time, as do the groans of both Maddoxes. </p>
<p>In a move directly mirroring what’s occurring on screen, Maddox presses a hand over her mouth and leans in close. “You’re mine, Jailyn,” both men whisper. “I knew it from the moment you were born.” Their hips move in tandem, the relentless rhythm identical.</p>
<p>It only takes a few minutes for the man in the recording to shudder and fill the young girl beneath him, his body unable to last long inside the tightest cunt he’s ever fucked. </p>
<p>Unfortunately for eighteen year old Jailyn, the man currently fucking her has had 16 years to build up his stamina. He alternates between hard, punishing thrusts of his hips and a slower rhythm, pushing in as far as possible before pulling back until just the tip of his cock is still sheathed inside her. After half an hour he still hasn’t cum, though they are both drenched in sweat and he’s panting with the need for release. The blue screen of the dvd menu casts a glow over their bodies, the homemade movie having ended quite some time ago. </p>
<p>The entire time he whispers a stream of filth into Jailyn’s ear, telling her about all the little girls and boys he’d fucked after her, and how none of them were as good as she was. </p>
<p>“I knew I had to have you again, but after your mother found out what had happened she moved you to the other side of the country, and I couldn’t find you.” He slows their pace down once again, catching his breath. “It took me years to find you, but you were worth the wait.” He kisses her softly, running his tongue across her bottom lip once before pulling back. </p>
<p>Jailyn’s eyes are vacant as she stares at the ceiling, doing her best to shut out everything happening around her. Maddox frowns when he sees that she’s no longer paying attention. His hips come to a halt and he brings a hand to her chin, gripping roughly once again until she meets his gaze. </p>
<p>“That’s much better. It’s rude to ignore the man who’s giving you exactly what you’ve been begging for for the last year and a half. I think you owe me an apology Jailyn.” When she stubbornly remains silent he laughs quietly, shaking his head. “You used to be such a good girl for me, I’m disappointed. And you’ve stopped screaming for me too. Have you already grown bored of me fucking you?” </p>
<p>He pulls out of her cunt and repositions his cock a little lower. “Well, I’ll just have to try something new to get a reaction out of you, won’t I?”</p>
<p>Jailyn’s eyes go wide as she feels the head of his cock press against her asshole. “No! Stop, I’ll do whatever you want, please!”</p>
<p>Maddox stills, putting only the barest hint of pressure against her hole now. “There she is! That’s the slut I know and love.” The hand gripping her chin loosens, his thumb stroking over her cheek, smudging the tear tracks there. “You used to beg me for my cock, you’ve been gagging for it since you were two years old, I know you’ve missed it.” He brings his free hand between her legs and rubs her clit gently. “Beg for it again,” he orders.</p>
<p>Jailyn’s harsh breathing fills the room as her body responds to the feeling of Maddox’s fingers, small shudders wracking her body as he brings her closer and closer to orgasm. “Please, fuck me,” she whispers, voice shaky, “please Maddox.”</p>
<p>An indulgent grin crosses his face as she speaks, his fingers rubbing faster. “You know better than that, Jailyn. What did I tell you to call me when I’ve got you spread out and begging in my bed?”</p>
<p>A sob escapes as she tries to grind down on his hand, ashamed at her body’s reaction but unable to stop chasing her orgasm. “Daddy!” she cries out. “Fuck me, Daddy!”</p>
<p>Maddox grins widely and watches hungrily as his hand sends her over the edge and her orgasm crashes over her entire body. As her loud moans fill the room he grips her hips and pushes into her ass, bottoming out  in a single hard thrust. Her moan sharply turns into a scream as he splits her open.</p>
<p>The feeling of her hole gripping him as tightly as her cunt did 16 years ago combined with her desperate screams cause his own orgasm, and he thrusts mindlessly until his cock has finally stopped pulsating inside her. Finally spent, Maddox collapses onto her shaking body, making sure to keep his softening cock in her as long as possible. Jailyn is thrashing once more underneath him, but his weight easily keeps her pinned. When he’s caught his breath again he finally rolls off of her, already missing the tight clutch of her body.</p>
<p>Jailyn is crying, pulling at her bindings until both wrists and ankles are chafed and bleeding.</p>
<p>Maddox reaches into the bedside table and pulls out another silk scarf and a roll of duct tape. He quickly stuffs the scarf into her mouth before slapping a piece of tape over her lips. “We’ve got two entire days together, I’d hate for someone to overhear.” He grabs the remote that he’d tossed aside earlier. “And besides, you definitely don’t want to miss the next video.” </p>
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